Dimethyl Sulfoxide → Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate

HRID 2368101노트

반응식

HRID 2368101 반응식
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.CS(C)=O>O>[O:1]=[CH:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1

참가 물질

5

반응물 3

HCID 679Dimethyl Sulfoxide2회HCID 8471TriethylamineHCID 57517495Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

생성물 1

HCID 57517496Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate수율 68.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate (6.33 g), triethylamine (15.9 mL) and dimethyl sulfoxide (30 mL) were added dropwise a mixture of sulfur trioxide pyridine complex (10.8 g) and dimethyl sulfoxide (30 mL) at room temperature, and the obtained mixture was stirred at room temperature for 1 hr. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with 1M hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.28 g).

후처리

  1. additionwere added dropwise
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1M hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-80f163d2f83b40fda80472bb07487570
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703758B2

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